Regioselective Enzymatic β‐Carboxylation of para‐Hydroxy‐ styrene Derivatives Catalyzed by Phenolic Acid Decarboxylases. Issue 8 (2nd April 2015)

• Record Type: Journal Article
• Authors: Wuensch, Christiane; Pavkov‐Keller, Tea; Steinkellner, Georg; Gross, Johannes; Fuchs, Michael; Hromic, Altijana; Lyskowski, Andrzej; Fauland, Kerstin; Gruber, Karl; Glueck, Silvia M.; Faber, Kurt
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 8(2015)
• Page Start: 1909
• Page End: 1918
• Publication Date: 2015-04-02
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201401028
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>We report on a 'green' method for the utilization of carbon dioxide as C₁ unit for the regioselective synthesis of (<italic>E</italic>)‐cinnamic acids <italic>via</italic> regioselective enzymatic carboxylation of <italic>para</italic>‐hydroxystyrenes. Phenolic acid decarboxylases from bacterial sources catalyzed the β‐carboxylation of <italic>para</italic>‐hydroxystyrene derivatives with excellent regio‐ and (<italic>E</italic>/<italic>Z</italic>)‐stereoselectivity by exclusively acting at the β‐carbon atom of the CC side chain to furnish the corresponding (<italic>E</italic>)‐cinnamic acid derivatives in up to 40% conversion at the expense of bicarbonate as carbon dioxide source. Studies on the substrate scope of this strategy are presented and a catalytic mechanism is proposed based on molecular modelling studies supported by mutagenesis of amino acid residues in the active site.</p> <p> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgjng09j5t" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </p> </abstract>